Methanol → Ammonium Hydroxide

HRID 353255

Reaction equation

HRID 353255 reaction equation
Cl.[NH:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[CH3:8][CH2:9][N:10]([CH2:13][CH3:14])[CH2:11]C.FC(F)(F)C(O[C:20](=[O:25])[C:21]([F:24])([F:23])[F:22])=[O:18].CO>C(Cl)Cl>[NH4+:2].[OH-:18].[F:24][C:21]([F:22])([F:23])[C:20]([N:2]1[CH2:7][CH2:6][NH:5][CH:4]([CH2:11][N:10]2[CH2:13][CH2:14][CH2:8][CH2:9]2)[CH2:3]1)=[O:25]

Participants

7

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 82044Piperazine, hydrochloride (1:?)

Product 2

HCID 14923Ammonium HydroxideYield 28%HCID 227071264-Trifluoroacetyl-2-(r,s)-(1-pyrrolidinyl)methyl piperazine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of (R,S)2-(1-pyrrolidinyl)methyl]piperazine hydrochloride (1.0 g, 3.58 mmol) and Et3N (0.5 mL, 3.58 mmol) in 10 mL of CH2Cl2 was added trifluoroacetic anhydride (0.5 mL, 3.58 mmol) at 0° C. The reaction mixture is stirred at 0° C. for 5 h. The reaction mixture was evaporated under reduced pressure (due to the water solubility of this compound there was no aqueous work-up) and isolated on a silica gel column (solvent system: CH2Cl2: CH3OH: 28% NH4OH (98:2:2) to give the desired product as a free base (0.18 g, 20%); 1H NMR (free base 200 MHz, CDCl3) d 1.76 (m,4H), 2.25-3.15 (m, 10H), 3.26 (t, 2H), 3.88 (m, 1H), 4.39 (t, 1H).

Workup

  1. customThe reaction mixture was evaporated under reduced pressure (due to the water solubility of this compound there
  2. customisolated on a silica gel column (solvent system

Sources & evidence

ORD record
ord-afbdb6e0852c4d6b9a5d57ce6b0a2957
Source dataset
uspto-grants-2004_06
Patent number
US06750216B2

Linked notes

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